Water → Perindopril

HRID 273477Notes

Reaction equation

HRID 273477 reaction equation
[CH3:1][CH2:2][CH2:3][C@H:4]([NH:10][C@H:11]([C:13]([N:15]1[C@@H:23]([C:24]([O:26]CC2C=CC=CC=2)=[O:25])[CH2:22][C@H:21]2[C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:14])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].O>C1CCCCC1.[Pd]>[CH3:1][CH2:2][CH2:3][C@H:4]([NH:10][C@H:11]([C:13]([N:15]1[C@H:23]([C:24]([OH:26])=[O:25])[CH2:22][C@H:21]2[C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:14])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 962WaterHCID 71751530(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid Benzyl Ester

Product 1

HCID 107807Perindopril

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8078CyclohexaneSolvent

Procedure

The Perindopril benzyl ester (20 g, 0.0436 moles) was dissolved in cyclohexane (80 ml) in a round bottom flask and the resulting solution was transferred into a hydrogenation bottle. To this was added 10% Palladium on carbon (10% loading), followed by water (70 ml). The reaction mixture was hydrogenated at 27° C. for 3 hrs, under 60 psi pressure when the reaction was complete. The reaction mixture was filtered off and the residue was washed with cyclohexane (20 ml). The filtrate was allowed to settle for 15 min. The aqueous phase was separated. It was washed with cyclohexane (20 ml, twice). Perindopril was isolated in an amount of 11.5 g (71.5%) from the aqueous layer by freeze drying.

Workup

  1. filtrationThe reaction mixture was filtered off
  2. washthe residue was washed with cyclohexane (20 ml)
  3. waitto settle for 15 min
  4. customThe aqueous phase was separated
  5. washIt was washed with cyclohexane (20 ml

Sources & evidence

ORD record
ord-d43390b073ae43a1b585a6872cc18615
Source dataset
uspto-grants-2008_11
Patent number
US07456296B2

Reaction notes

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